Vollhardt et al., J. Am. Chem. Soc., vol 96 (1974), pages 4996-4998, have disclosed the synthesis of 4-hydroxymethylbenzocyclobutene by a cyclization process, which gives a 14% yield of the desired product.
Wong (U.S. Pat. No. 4,708,994) has proposed using 4-hydroxymethylbenzocyclobutene to treat engineering thermoplastics, which may then be crosslinked and cured by heating above about 200.degree. C.
Skorcz (U.S. Pat. No. 3,408,391) has recited the preparation of 1-hydroxymethylbenzocyclobutene by reducing benzocyclobutene-1-carboxylic acid with lithium aluminum hydride in an anhydrous reaction medium, such as ether or tetrahydrofuran. The intermediate complex alcoholate is hydrolyzed by treatment with an acid to produce 1-hydroxymethylbenzocyclobutene.
Wilson (U.S. Pat. No. 3,859,364) has proposed reducing indane esters using lithium aluminum hydride.
Vanderwerff (U.S. Pat. No. 3,288,823) has proposed reducing 2,6-naphthalenedicarboxaldehyde to 2,6-bis(hydroxymethyl)naphthalene using excess sodium borohydride in ethanol.
Chaikin et al., J. Am. Chem. Soc., vol. 71 (1949), pages 122-125, have summarized the reduction of aldehydes and ketones by sodium borohydride in aqueous or methanolic solutions.
Ipatieff et al. (U.S. Pat. No. 2,694,730) has recited reduction of 2-formyl-6-hydrocarbylbicyclo-[3.2.1]-2-octenes to corresponding 2-alcohols by catalytic hydrogenation.